My plan is to use my VA benefit to buy a duplex, live on one side and rent the other side as well as rent out our condo.

It's one thing to live in the flip while YOU are the one making the money and saving the taxes, but its entirely different to be living in a big mess with no benefit.

In the event of a lawsuit where some lawyer tries to pierce the veil for liability purpose these two LLC's could be viewed as a single entity sharing funds.Ask your real estate attorney, but I suspect you could benefit from using a holding company LLC and then have the 10 LLC's as subsidiaries.

It was a huge benefit when I first started thinking about RE.

And make sure you have a comprehensive understanding of all the benefits that your service to the country will afford you, to include the VA loan that you're eligible for that may very well be what you use to get started as an investor.

Its hard for me to decide if I should let this house go because of the benefits holding properties have.

hmm;  Do you understand that PMI protects only the lender and there's no benefit to you????

As an added benefit, we will only have to file a Reg D filing once with the SEC and can use the same PPM, with a separate one page addendum for each note offering. 

However, once you have a tenant in place and with good landlording behavior, the tenant can request for voucher increase whereby you could benefit every year.If you would like to know more, ping me and I can share more of my section-8 experiences.

That's incentive enough to report erroneous expenses to reduce my MAGI as I may reap the benefits.